Phosgene → HCID 70650772, compound

HRID 1425651Notes

Reaction equation

HRID 1425651 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][NH2:13].[C:17](Cl)(Cl)=[O:18].[S:21]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[C:23]([OH:30])=[N:22]1>C1(C)C=CC=CC=1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][NH:13][C:23]([N:22]1[C:17](=[O:18])[C:24]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[S:21]1)=[O:30]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 16784344953883-20-0HCID 178519011HCID 178519011, compound

Product 1

HCID 70650772HCID 70650772, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-(furan-2-ylmethoxymethyl)benzylamine (218 mg, 1 mmol) in toluene (10 ml) is admixed at 25° C. with phosgene (5 ml, 10 mmol; 20% solution in toluene) and heated to reflux. After 3 h, the mixture is filtered and the filtrate is concentrated. The residue is taken up in THF (25 ml) and admixed with compound 1 (122 mg, 0.8 mmol). The mixture is stirred at 60° C. for 3 h. The reaction is monitored by HPLC-MS. The solvent is reduced, and the product crystallizes. C20H17N3O4S, Mw 395.44. Yield: 239 mg (75.7%).

Workup

  1. temperatureheated to reflux
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. customthe product crystallizes

Sources & evidence

ORD record
ord-33b402a821bf4ff78fececfb49c0014c
Source dataset
uspto-grants-2015_01
Patent number
US08933024B2

Reaction notes

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